DE365682C - Process for the preparation of the acetyl compounds of the quinine esters of aromatic oxycarboxylic acids - Google Patents

Process for the preparation of the acetyl compounds of the quinine esters of aromatic oxycarboxylic acids

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Publication number
DE365682C
DE365682C DEF49269D DEF0049269D DE365682C DE 365682 C DE365682 C DE 365682C DE F49269 D DEF49269 D DE F49269D DE F0049269 D DEF0049269 D DE F0049269D DE 365682 C DE365682 C DE 365682C
Authority
DE
Germany
Prior art keywords
quinine
esters
preparation
oxycarboxylic acids
aromatic oxycarboxylic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DEF49269D
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German (de)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Farbenfabriken Vorm Friedr Bayer and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Farbenfabriken Vorm Friedr Bayer and Co filed Critical Farbenfabriken Vorm Friedr Bayer and Co
Priority to DEF49269D priority Critical patent/DE365682C/en
Application granted granted Critical
Publication of DE365682C publication Critical patent/DE365682C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Darstellung der Acetylverbindungen der Chininester . aromatischer Oxycarbonsäuren. Es wurde gefunden, .daß man die Chininester aromatischer Oxvcarbonsäuren durch Behandeln mit acetylierenden Mitteln leicht und mit guter Ausbeute in ihre Acetylverbindungen überführen kann, denen insofern wertvolle therapeutische Eigenschaften zukommen, als sie statt der zu erwartenden temperaturherabsetzenden Wirkung Temperatursteigerung hervorrufen.Process for the preparation of the acetyl compounds of the quinine esters. aromatic oxycarboxylic acids. It has been found that the quinine esters are more aromatic Oxvcarboxylic acids by treating with acetylating agents easily and with good Yield can be converted into their acetyl compounds, which in this respect are valuable therapeutic Properties come as they instead of the temperature-reducing ones to be expected Effect causing temperature increase.

Stellt man die neuen Verbindungen mit Hilfe von ACeti'IChlorid dar, so erhält man durch. Umsetzung von ein Molekül der Chininester mit ein Molekül Acetylchlorid ihre salzsauren Salze, die in Wasser schwer löslich und fast geschmacklos sind.If the new compounds are represented with the help of ACeti'IChlorid, so you get through. Reaction of one molecule of the quinine ester with one molecule of acetyl chloride their hydrochloric acid salts, which are sparingly soluble in water and almost tasteless.

Beispiel i.Example i.

Zu einer abgekühlten Lösung von 442 Gewichtsteilen Salicylsäurechininester' (Patentschrift 137207) in 2 ooro Volumteilen Tetrachlorkohlenstoff werden unter Kühlen und Rühren 78,5 Gewichtsteile Acetylchlorid gegeben und das Gemisch dann bei gewöhnlicher Temperatur stehengelassen. Nach kurzer Zeit beginnt die Ausscheidung des salzsauren Acet;rIsalicylsäurechininesters, der nach eintägigem Stehen abgeaugt wird. Die Ausbeute beträgt 95 bis 96 Prozent der Theorie. Zur Reinigung kann, das Salz aus 7 bis 8 Ggwichtsteilen Alkohol umkristallisiert werden. Es bildet dann weiße Blättchen, die bei 240 bis 241' unter Zersetzung schmelzen. Zur Gewinnung des freien Esters schüttelt man das Salz mit Sodalösung und Benzol bis zur vollständigen Lösung, trennt und destilliert das Benzol vollständig ab. Der Acetylsalicylsäurechininester bleibt als helles Harz zurück, das nach längerem Trocknen bei go bis loo° hart und pulverisierbar wird. .78.5 parts by weight of acetyl chloride are added to a cooled solution of 442 parts by weight of quinine salicylate (patent specification 137207) in 2 ooro parts by volume of carbon tetrachloride, with cooling and stirring, and the mixture is then allowed to stand at ordinary temperature. After a short time, the excretion of the hydrochloric acid acetate; risalicylic acid quinine ester begins, which is absorbed after standing for one day. The yield is 95 to 96 percent of theory. For cleaning, the salt can be recrystallized from 7 to 8 parts by weight of alcohol. It then forms white platelets which melt at 240 to 241 'with decomposition. To obtain the free ester, the salt is shaken with soda solution and benzene until it is completely dissolved, and the benzene is separated off and completely distilled off. The acetylsalicylic acid quinine ester remains as a light-colored resin, which becomes hard and pulverizable after prolonged drying at between 0 and 100 °. .

Beispiel 2.Example 2.

loo Gewichtsteile m Kresotinsäurechininester (aus Ligroin weiche, weiße Blättchen vom Schmelzpunkt 1q.5°) werden zwei Stunden mit Zoo Gewichtsteilen Essigsäureanhydrid zum schwachen Sieden erhitzt. Nachdem Erkalten wird dass überschüssige Essigsäureanhydrid mit Wasser zersetzt, die erhaltene Lösung mit Sodalösung und Benzol geschüttelt, getrennt und das Benzol abdestilliert. Der zurückbleibende Acetyl - m - Kresotinsäurechininester erstarrt schnell und wird aus einer Mischung von Benzol und Ligroin umkristallisiert. Er bildet kleine derbe weiße Kristalle, die bei 16g° schmelzen, und vollständig geschmacklos sind.loo parts by weight m quinine cresotinate (from ligroin soft, white flakes with a melting point of 1q.5 °) are treated with zoo parts by weight for two hours Acetic anhydride heated to a gentle boil. After cooling down, that becomes excess Acetic anhydride is decomposed with water, the resulting solution with soda solution and Benzene shaken, separated and the benzene distilled off. The remaining acetyl - m - Quininic cresotinate solidifies quickly and is made from a mixture of Benzene and ligroin recrystallized. It forms small, coarse white crystals that Melt at 16g °, and are completely tasteless.

Bringt man den m Kresotinsäurechininester nach der im Beispiel i beschriebenen Weise mit AcetyIchlorid zur Umsetzung, so gewinnt man das salzsaure Salz des Acetvl-m-Kresotinsäurechininesters, das aus Aceton in weißen glänzenden Blättchen kristallisiert, die bei z34.° unter Zersetzung schmelzen. Es ist in Wasser schwer löslich und fast geschmacklos.Bringing the m quininic cresotinate according to that described in Example i way with acetyl chloride for implementation, the hydrochloric acid is obtained Salt of Acetvl-m-cresotinic acid quinine ester, which is obtained from acetone in white glossy The flakes crystallize and melt at z34 ° with decomposition. It's in water difficult to dissolve and almost tasteless.

Claims (1)

PATENT-ANsPRÜc13: Verfahren zur Darstellung der Acetylverbindungen der Chininester aromatischer Oxycarbonsäuren, darin bestehend, daß man diese Ester mit acetylierendenMitteln behandelt.PATENT-ANsPRÜc13: Process for the preparation of the acetyl compounds the quinine esters of aromatic oxycarboxylic acids, consisting in that one of these esters treated with acetylating agents.
DEF49269D 1921-05-10 1921-05-10 Process for the preparation of the acetyl compounds of the quinine esters of aromatic oxycarboxylic acids Expired DE365682C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF49269D DE365682C (en) 1921-05-10 1921-05-10 Process for the preparation of the acetyl compounds of the quinine esters of aromatic oxycarboxylic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF49269D DE365682C (en) 1921-05-10 1921-05-10 Process for the preparation of the acetyl compounds of the quinine esters of aromatic oxycarboxylic acids

Publications (1)

Publication Number Publication Date
DE365682C true DE365682C (en) 1922-12-21

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ID=7102878

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF49269D Expired DE365682C (en) 1921-05-10 1921-05-10 Process for the preparation of the acetyl compounds of the quinine esters of aromatic oxycarboxylic acids

Country Status (1)

Country Link
DE (1) DE365682C (en)

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